The search for the leaders who will take your company to the next level is worth the investment. (BCV)

How To Hire Your First Leadership Team

There’s a lot at stake when you’re making your first leadership hires. Follow these steps to determine the right leaders for your early-stage startup.

9 min read October 24, 2023
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For early-stage founders, nailing your first leadership hires is key. There’s a lot at stake when you’re hiring the people responsible for building out the functional areas of your company — your business, your company culture, the future.

In my work at BCV, I advise our founders on how to successfully scale their organizations and capitalize on our extensive talent network. Before I joined BCV, I worked at three hypergrowth-stage companies: Dropbox, MuleSoft and TripActions. At each of those companies, I was there when we scaled from hundreds to thousands of employees in a very short period of time. And because of that, I spent a lot of time thinking about people infrastructure and the all-important question: How do you pick the right leaders for your organization at the right time?

As a startup founder, your job is to recruit a world-class team, and your C-suite will provide a foundation for taking your company to the next level. Using my own successes (and failures) in this arena, I’ll share a few of my key learnings that can help you as you approach your first leadership hires. 

Do your research

Let’s face it, when you’re making your first leadership hires, you’ll likely be interviewing candidates who have an incredible amount of experience on topics you’re not an expert in. 

Say you’re a technical founder. You probably have far fewer years of experience in marketing or sales than the people you’ll be interviewing to run those teams. Many early-stage founders we see are early in their careers, and it can feel intimidating to interview people who have so much more experience than you have in a particular topic, and in-depth knowledge of a function that you may or may not have much exposure to. It’s a humbling experience. 

It can be tempting to leap straight into recruiting, but the founders who make early hires the best are the ones who do their homework ahead of time. In practice, this looks like going out and finding five candidates the trusted people in your network think are amazing. These are the kinds of people who you wish you could recruit, but probably can’t because they’re either so good at what they do or have a little more experience than what you’d be looking to hire for. 

Your goal is not to hire these people. Instead, you’re on a fact-finding mission, and your goal is to take a call with each of these people to uncover what “great” looks like. In the course of your conversations with each of them, you should better understand the caliber of talent that you should be looking for when you do go out to hire for the role. Ask questions that help you uncover: What makes them tick? What kind of opportunity would attract them away from the work they’re doing today? What traits would they look for in a CEO? What red flags should you watch out for when you’re interviewing someone for a CTO or CMO role?

When I joined TripActions, I was tasked with hiring the entire people leadership team — aka go recruit an entire team of people that have more in-depth knowledge in their function than you do. I didn’t have deep expertise in any of those functions, but I had to go out and find the experts and hire them. 

I used this approach for the hardest of the roles, head of total rewards, which includes overseeing compensation and benefits. I reached out to the five best HR leaders I knew and asked them to refer me to the best total rewards leader they knew, and then took those leaders to (sometimes virtual) coffee. This allowed me to get to know them a bit, refine my recruiting approach for the role, and most importantly, define the bar for what I should be looking for. I didn’t hire (read: wasn’t able to hire) any of them, but they all sent me referrals and acted as resources throughout my process. One of them even helped me do a final round interview as I was deciding on a candidate. 

So much value came out of a set of activities that on the surface may not seem to be directly related to actual recruiting but proved to be invaluable to the process, and I recommend you try a similar approach. 

These conversations won’t just inform your hiring process. You’ll also do a better job assessing candidates and will waste a lot less of your time down the line than if you’d jumped in and started interviewing candidates without doing some research. 

Be strategic and practical about your search

Founders doing their first executive searches often want to leverage their networks for their searches for as long as they can. This isn’t a bad strategy — you should ask your investors, friends, past colleagues, etc. for referrals, see who they know, and reach out to the people in your network. 

But the reality is that many times these searches end up getting sent to a search firm. Be warned that this approach usually leads to sticker-shock — many of these very senior searches can cost more than $100,000 each. But what you’re paying for, however, is someone who knows the talent pool inside and out and, since time is money, they can expedite the process of getting a great hire in the door for you. 

Give yourself a timeline to make a hire on your own, but be practical. At a certain point, there’s a cost to not having a leader you need at your company, and at some point you may need to hire that search firm. The value of someone being in a leadership role as soon as possible for an early-stage company is really high. If you need a VP of sales, you want them there as soon as possible, because every moment they’re working with you can have a tangible impact on your business. As you well know, startup time moves so differently than time at a big company, and so much can happen in just a month.

One of our portfolio companies recently experienced this. The team is hiring a CFO with a search firm and a chief people officer without a firm. The founder agreed we’d give it two months to source the CPO without a firm and if we didn’t have major traction by then, we’d bring in a search firm. By time-bounding your search with a deadline, you give yourself an opportunity to pull the cord and get the help you need. Don’t let your search drag out too long — time has a cost.

And don’t think you need to go alone on this — our team works very closely with founders on searches even before they’re officially searches and can help you set the strategy, advise on profile and set you up with the very best search firms given your search perimeters. Reach out early and reach out often. You don’t need to be an expert in exec search, that’s what we’re here for.

Not all ‘firsts’ are created equal

Don’t expect the first functional leaders you hire to be the same — they won’t have the same profile, background or years of experience. And that’s OK. You need to hire leaders who are going to be excellent at their job for the next 18 to 24 months, with the hope that they can grow and scale themselves into the next phase of the company. And what each function needs for that time period looks very different depending on the maturity of your business and your priorities and goals for each function.

Thinking about your leadership roles years down the line just doesn’t make sense for an early-stage company — businesses change so quickly that if you try to hire someone who will help your company five years from now, you may be overlooking a great person who can help your company today. You’re likely to hire someone that either has way too much experience or is comfortable at a much different scale from the one that you’re at right now. 

It can be tempting to look at each leadership hire in a silo. But the reality is, what you decide you need in a head of X will depend on the other people you have sitting around the table. Not every leadership hire is going to be equal in terms of the type of experience they bring to the table, the number of years of work experience they have, or whether they’ve done their job before at a different organization. 

Your first VP of marketing may not be equal in experience to your first VP of finance, who may not be equal to your first VP of sales. Maybe you’re heading towards an exit, and so you’re ready for a very experienced CFO to guide you there, but at the same time you keep more of an up-and-comer in your people role because you feel confident that, surrounded by an experienced CFO and GC, you can support them. 

Bottom line: Before you kick off a new role, look at the entire team before you dive into the role. You’re building a team that works as a unit, not just hiring an individual.

Building a foundation for what’s next

Getting a feel for what your company needs at a specific stage, along with knowing when to leverage your network and when to pay for more access to talent are going to help guide you to building a best-in-class leadership team that can take you where you need to go — whether you’re starting from scratch or preparing for an IPO.

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